[The following is an excerpt from my second book, Goodwill Tour: Paying It Forward. You can order the entire paperback or ebook at amazon.com/Goodwill-Tour-Forward.]

“Goodwill Tour” first stop: Memphis, TN

Despite neither of us being morning people, we woke up early on Tuesday, July 19^th, raring to go after a sleepless night. While Emily finished packing, I took her 2008 Chevy Trailblazer, nicknamed Levi, down the street for a quick interior vacuum. We then loaded suitcases, coolers, camping gear and a ton of snacks for the road.

Before we had time to second-guess this somewhat whimsical trip with a relative stranger, Emily and I were well on our way south on Interstate-71. Driving down the road with an odd mixture of excitement and trepidation, a quote from Bill Bryson’s A Walk in the Woods came to mind:

I had waited for months for this day…I wanted to see what was out there. All over America today people would be dragging themselves to work, stuck in traffic jams, wreathed in exhaust smoke. I was going for a walk in the woods.

Well, we weren’t going for a walk in the woods—and I had waited for this day for years, not months—but you get the idea. This was either an asinine pipedream or the adventure of a lifetime.

Due to traffic delays, we didn’t arrive in Memphis until about 7:00 p.m. Emily decided we would spend the first few nights in a hotel, as it was extremely hot, and we didn’t know anyone in Memphis to put us up. Though not a couple—let me nip that in the bud from the start—we’d agreed early in our planning that sharing a room made far more sense economically. Our downtown hotel, the Crowne Plaza, gave us great access to the heart of the city and we headed straight to the trolley for a look around.

The trolley was immaculate! Shiny, antique wooden benches and windows, the latter opened to allow in a welcome breeze, gave the car a vintage décor. Excluding one man, Emily and I took advantage of this good fortune as the only passengers by taking our first pictures of the trip.

Stepping off the trolley, the thought hit me: We are really doing this! Em and I have the next several days to do whatever we want, to travel and live on our own schedules without the stress and responsibility of the so-called real-world.

In the morning, Emily and I decided to heed several friends’ suggestions and took the $4 monorail to Mud Island River Park. On the ride over, a female staff member dressed in khakis and a bright red Mud Island polo shirt greeted us. Being the lone passengers at the time, Emily asked the attendant, “Are you our entertainment?” Without hesitation, our host did an impromptu dance for us.

We could tell immediately that Jena was an affable young lady who didn’t waste time complaining about the 100-degree temperature. When questioned about her favorite part of the job, she said it was being able to meet people from all over the world, from Amsterdam to Hawaii. Her favorite thing about Memphis: “Beale Street. There are so many places to go and eat, to hear live music. It’s always live.”

Jena could have been in a foul mood, outside in excessive heat. Instead, she had a big smile for everyone, asked questions, and seemed genuinely interested in our responses.

Since two cars shuttled visitors to and from Mud Island, we told our new friend that we would catch her train on the way back (which she told us was the car that Tom Cruise had ridden during the chase scene in the movie The Firm). As we got off the rail, I hinted strongly to Emily that we’d just met our first donation recipient.

While we put the idea on the back burner, Em and I explored Mud Island. Had the temperature been 25 degrees cooler, the park would have been the ideal setting for a picnic. We saw several young adults singing and dancing, oblivious to the hotness. The sun shimmered on the Mississippi and a light breeze lifted from the water from time to time. It was a beautiful day in Memphis, with blue skies and few clouds.

When we stood by to return from the island, a staff member told us Jena was on her break for the next 45 minutes. We decided to wait. After all, we’d promised we would see her again.

So we plotted.

Giving money to a stranger was foreign to us. We didn’t know how to give cash to a person we had just met. Even Emily, who seems comfortable in any situation, was nervous.

I suggested we pose the idea to Jena as if we were conducting a survey, asking strangers what they would do if someone gave them $100. (Unlike the donations to come, this was not necessarily a pay-it-forward gift: One of Emily’s co-workers had donated $100 to be used specifically in Memphis, as her family had lived there years ago when her husband was in the military.)

Soon enough, we saw Jena again. She remembered our names, which impressed us, as she probably saw hundreds of people every day. Jena looked suspicious: “They told me y’all wouldn’t get back on without me.”

Emily: “Well, we told you that we’d see you on our way back.”

I dipped my toe in: “Yeah, we’ve been walking around asking people this question, ‘What would you do if someone just walked up and gave you $100?’”

Without hesitation, Jena replied: “The staff is not permitted to accept tips.”

I tried again: “No, no, no. I’m just saying hypothetically. What if someone gave you $100?”

Without a second’s pause, Jena answered: “I have four kids. I’d give them each $25.”

Emily and I changed the subject and hid our smiles.

Worried Jena might be prohibited from taking our gift, we decided we should talk to her boss. After getting our picture taken with Jena, we told her goodbye, acting like we’d never see her again. When I got to the ticket booth, I asked to see the manager about one of the staff members.

The woman behind the desk shot back, “What did he or she do wrong?”

I clarified that it was quite the opposite. We wanted to reward Jena for her great attitude.

As the woman paged the manager, she said: “Well, you picked a good one. Jena sometimes goes across the street and shares her lunch with the homeless people.”

Two men came out of a back office and asked me how they could help. I explained that Emily and I were doing a “goodwill tour” of several cities and wanted to give money to deserving people. I told them how great of a job Jena was doing and that we were not giving her a tip, but a surprise gift as part of our project. They agreed that Jena was a great choice and asked only that we give her the money offsite.

One of the men radioed for Jena to come down to the office. A few seconds later, she saw Emily and me with her boss and gave us a “what-the-hell-is-going-on?” half-grin. Her boss asked Jena to go across the street with us and get him a newspaper. Hesitantly, she walked with us. I can’t imagine what was going on in her head at this point.

I broke the ice: “Remember that $100 we talked about on the monorail, Jena? Well, we want to give it to you. We are traveling around, meeting special people and giving money away. After meeting you and seeing what a great job you do, we want you to be our first selection.”

Jena was shocked, and tears welled up in her eyes, which caused a chain-reaction in Emily and me. She couldn’t believe strangers as of a few hours ago were giving her money. Jena said she couldn’t wait to share the joy with her kids. She informed us that she is 26 and the mother of three boys and a girl, ages one, four, five and eight.

Giving Jena the money felt great (though the credit goes to Emily’s co-worker Nancy for her generous contribution). It was an emotional experience, and we seesawed between nervous laughter and happy tears. Jena sighed, “Today, I am truly blessed.”

After more hugs and pictures, Emily and I had to move on. Relieved that our opening donation went better than we could have imagined, we were able to relax. Maybe this crazy plan would work out after all. The trip was off to a great start.